My ex-boyfriend and I have been broken up for six years now, but we remain very good friends. I have always had a little crush on his roommate, and just recently we talked about the possibility of taking our relationship to the next level. My ex and I have both dated other people since our split, but is dating his best friend and roommate just totally not allowed? Should I wait until he eventually moves out? — Proceeding Cautiously Cassie
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Dear Proceeding Cautiously Cassie,
Six years is a long time to be broken up with your ex, and while I think it's great that you remain good friends, I think it's high time you move on with your life. Dating his best friend might be a little too close for comfort, but who knows, he might be totally OK with the idea! Before taking this friendship to the next level, I'd talk to your ex about it first and find out where he stands. If he's all for it, great, but if he's opposed, you're going to have to ask yourself which relationship is more important to you. I hope it works out for everyone involved, and good luck to you!